Dynamic kinetic asymmetric transformation of diene monoepoxides: A practical asymmetric synthesis of vinylglycinol, vigabatrin, and ethambutol

…, RC Bunt, RC Lemoine, TL Calkins

Index: Trost, Barry M.; Bunt, Richard C.; Lemoine, Remy C.; Calkins, Trevor L. Journal of the American Chemical Society, 2000 , vol. 122, # 25 p. 5968 - 5976

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Citation Number: 207

Abstract

The ability to perform a dynamic kinetic asymmetric transformation (DYKAT) using the palladium-catalyzed asymmetric allylic alkylation (AAA) is explored in the context of butadiene monoepoxide. The versatility of this commercially available, but racemic, four- carbon building block becomes significantly enhanced via conversion of both enantiomers into a single enantiomeric product. The concept is explored in the context of a synthesis of ...